SU1627087A3 - Способ получени диастереомера N- @ 4-[2-(2-амино-4-гидрокси-5,6,7,8-тетрагидропиридо[2,3- @ ]пиримидин-6-ил)этил]бензоил @ -L-глутаминовой кислоты со значением [ @ ] @ -21,06 @ или диастереомера N- @ 4-[2-(2-амино-4-гидрокси-5,6,7,8-тетрагидропиридо[2,3- @ ]пиримидин-6-ил)этил]бензоил @ -L-глутаминовой кислоты со значением [ @ ] @ +31,09 @ или их фармацевтически приемлемых солей с основанием - Google Patents
Способ получени диастереомера N- @ 4-[2-(2-амино-4-гидрокси-5,6,7,8-тетрагидропиридо[2,3- @ ]пиримидин-6-ил)этил]бензоил @ -L-глутаминовой кислоты со значением [ @ ] @ -21,06 @ или диастереомера N- @ 4-[2-(2-амино-4-гидрокси-5,6,7,8-тетрагидропиридо[2,3- @ ]пиримидин-6-ил)этил]бензоил @ -L-глутаминовой кислоты со значением [ @ ] @ +31,09 @ или их фармацевтически приемлемых солей с основанием Download PDFInfo
- Publication number
- SU1627087A3 SU1627087A3 SU874202677A SU4202677A SU1627087A3 SU 1627087 A3 SU1627087 A3 SU 1627087A3 SU 874202677 A SU874202677 A SU 874202677A SU 4202677 A SU4202677 A SU 4202677A SU 1627087 A3 SU1627087 A3 SU 1627087A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- hydroxy
- diastereomer
- amino
- glutamic acid
- benzoyl
- Prior art date
Links
- 229960002989 glutamic acid Drugs 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 4
- 125000006239 protecting group Chemical group 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 239000004220 glutamic acid Substances 0.000 claims description 12
- -1 ethyl benzoyl Chemical group 0.000 claims description 10
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 3
- 235000013922 glutamic acid Nutrition 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 150000003278 haem Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- 238000000926 separation method Methods 0.000 abstract description 2
- ZUQBAQVRAURMCL-CVRLYYSRSA-N (2s)-2-[[4-[2-(2-amino-4-oxo-5,6,7,8-tetrahydro-1h-pyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoyl]amino]pentanedioic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2CC1CCC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 ZUQBAQVRAURMCL-CVRLYYSRSA-N 0.000 abstract 1
- 229940034982 antineoplastic agent Drugs 0.000 abstract 1
- 239000002246 antineoplastic agent Substances 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- RKOTXQYWCBGZLP-UHFFFAOYSA-N N-[(2,4-difluorophenyl)methyl]-2-ethyl-9-hydroxy-3-methoxy-1,8-dioxospiro[3H-pyrido[1,2-a]pyrazine-4,3'-oxolane]-7-carboxamide Chemical compound CCN1C(OC)C2(CCOC2)N2C=C(C(=O)NCC3=C(F)C=C(F)C=C3)C(=O)C(O)=C2C1=O RKOTXQYWCBGZLP-UHFFFAOYSA-N 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical group 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- MFEDKMBNKNOUPA-UHFFFAOYSA-N (2-bromo-4,7-dimethyl-3-oxo-7-bicyclo[2.2.1]heptanyl)methanesulfonic acid Chemical compound C1CC2(C)C(=O)C(Br)C1C2(CS(O)(=O)=O)C MFEDKMBNKNOUPA-UHFFFAOYSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- 241001260012 Bursa Species 0.000 description 1
- 101100135744 Caenorhabditis elegans pch-2 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010035226 Plasma cell myeloma Diseases 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 201000000050 myeloid neoplasm Diseases 0.000 description 1
- PIRWNASAJNPKHT-SHZATDIYSA-N pamp Chemical compound C([C@@H](C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)N)C(C)C)C1=CC=CC=C1 PIRWNASAJNPKHT-SHZATDIYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87153986A | 1986-06-06 | 1986-06-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1627087A3 true SU1627087A3 (ru) | 1991-02-07 |
Family
ID=25357673
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU874202677A SU1627087A3 (ru) | 1986-06-06 | 1987-06-05 | Способ получени диастереомера N- @ 4-[2-(2-амино-4-гидрокси-5,6,7,8-тетрагидропиридо[2,3- @ ]пиримидин-6-ил)этил]бензоил @ -L-глутаминовой кислоты со значением [ @ ] @ -21,06 @ или диастереомера N- @ 4-[2-(2-амино-4-гидрокси-5,6,7,8-тетрагидропиридо[2,3- @ ]пиримидин-6-ил)этил]бензоил @ -L-глутаминовой кислоты со значением [ @ ] @ +31,09 @ или их фармацевтически приемлемых солей с основанием |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0248573A3 (da) |
| JP (1) | JPH07116190B2 (da) |
| KR (1) | KR950004894B1 (da) |
| CN (1) | CN1019391B (da) |
| AU (1) | AU592182B2 (da) |
| CA (1) | CA1301155C (da) |
| DK (1) | DK170023B1 (da) |
| EG (1) | EG19551A (da) |
| ES (1) | ES2003828A6 (da) |
| GR (1) | GR870783B (da) |
| NZ (1) | NZ219971A (da) |
| PH (1) | PH25509A (da) |
| PT (1) | PT84990B (da) |
| SU (1) | SU1627087A3 (da) |
| ZA (1) | ZA873083B (da) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2133748C1 (ru) * | 1994-09-06 | 1999-07-27 | Кабусики Кайся Якулт Хонса | Производные камптотецина, способ их получения и противоопухолевая композиция |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE60038B1 (en) * | 1986-06-30 | 1994-05-18 | Univ Princeton | 4(3H)-oxo-5, 6, 7, 8-tetrahydropyrido-[2, 3-d]pyrimidine derivatives |
| GB8625019D0 (en) * | 1986-10-18 | 1986-11-19 | Wellcome Found | Compounds |
| US4895946A (en) * | 1987-10-26 | 1990-01-23 | The Trustees Of Princeton University | Process for the preparation of fused pyridine compounds |
| US4889859A (en) * | 1988-02-05 | 1989-12-26 | The Trustees Of Princeton University | Pyrido[2,3-d]pyrimidine derivatives |
| JP2830008B2 (ja) * | 1988-04-01 | 1998-12-02 | 武田薬品工業株式会社 | 縮合ピリミジン誘導体 |
| US5223620A (en) * | 1988-04-01 | 1993-06-29 | Takeda Chemical Industries, Ltd. | Pyrido[2,3-d]pyrimidine compounds useful as intermediates |
| DK172753B1 (da) * | 1988-05-25 | 1999-06-28 | Lilly Co Eli | N-(5,6,7,8-tetrahydropyrido[2,3--d]pyrimidin-6-yl-alkanoyl)-glutaminsyrederivater, deres anvendelse, farmaceutiske præparat |
| US5008391A (en) * | 1989-07-07 | 1991-04-16 | Eli Lilly And Company | Enantioselective synthesis of antifolates |
| US5066828A (en) * | 1990-04-12 | 1991-11-19 | Merrell Dow Pharmaceuticals Inc. | Difluoroglutamic acid conjugates with folates and anti-folates for the treatment of neoplastic diseases |
| EP1054859A4 (en) * | 1998-02-11 | 2003-03-05 | Lilly Co Eli | PROCESSES AND INTERMEDIATES USEFUL FOR THE MANUFACTURE OF ANTIFOLICS |
| CN110749692B (zh) * | 2019-10-15 | 2022-03-18 | 扬子江药业集团有限公司 | L-谷氨酸二乙酯盐酸盐及其光学异构体的分离检测方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA861235B (en) * | 1985-03-08 | 1986-10-29 | Univ Princeton | Pyrido(2,3-d)pyrimidine derivatives |
-
1987
- 1987-04-14 NZ NZ219971A patent/NZ219971A/xx unknown
- 1987-04-29 ZA ZA873083A patent/ZA873083B/xx unknown
- 1987-05-04 EG EG26087A patent/EG19551A/xx active
- 1987-05-06 DK DK232387A patent/DK170023B1/da not_active IP Right Cessation
- 1987-05-07 JP JP62109938A patent/JPH07116190B2/ja not_active Expired - Fee Related
- 1987-05-12 AU AU72731/87A patent/AU592182B2/en not_active Ceased
- 1987-05-19 GR GR870783A patent/GR870783B/el unknown
- 1987-05-22 EP EP87304580A patent/EP0248573A3/en not_active Withdrawn
- 1987-05-25 CA CA000537814A patent/CA1301155C/en not_active Expired - Lifetime
- 1987-06-02 PT PT84990A patent/PT84990B/pt not_active IP Right Cessation
- 1987-06-04 PH PH35342A patent/PH25509A/en unknown
- 1987-06-05 KR KR1019870005798A patent/KR950004894B1/ko not_active Expired - Fee Related
- 1987-06-05 SU SU874202677A patent/SU1627087A3/ru active
- 1987-06-05 ES ES8701666A patent/ES2003828A6/es not_active Expired
- 1987-06-06 CN CN87104103A patent/CN1019391B/zh not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| Грюштейн Дх., Виниц М. Хими аминокислот и пептидов.- М.: Мир, 1965, с.134. * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2133748C1 (ru) * | 1994-09-06 | 1999-07-27 | Кабусики Кайся Якулт Хонса | Производные камптотецина, способ их получения и противоопухолевая композиция |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA873083B (en) | 1987-10-26 |
| NZ219971A (en) | 1989-08-29 |
| GR870783B (en) | 1987-09-25 |
| PT84990A (en) | 1987-07-01 |
| KR950004894B1 (ko) | 1995-05-15 |
| CN87104103A (zh) | 1987-12-30 |
| AU7273187A (en) | 1987-12-10 |
| JPH07116190B2 (ja) | 1995-12-13 |
| ES2003828A6 (es) | 1988-11-16 |
| KR880000431A (ko) | 1988-03-25 |
| PH25509A (en) | 1991-07-24 |
| EG19551A (en) | 1996-02-29 |
| PT84990B (pt) | 1990-03-08 |
| CN1019391B (zh) | 1992-12-09 |
| EP0248573A2 (en) | 1987-12-09 |
| CA1301155C (en) | 1992-05-19 |
| AU592182B2 (en) | 1990-01-04 |
| DK170023B1 (da) | 1995-05-01 |
| DK232387D0 (da) | 1987-05-06 |
| EP0248573A3 (en) | 1989-06-14 |
| DK232387A (da) | 1987-12-07 |
| JPS6339878A (ja) | 1988-02-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| REG | Reference to a code of a succession state |
Ref country code: RU Ref legal event code: MM4A Effective date: 20050606 |